Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

José M Gil-Negrete; José Pérez Sestelo; Luis A Sarandeses

doi:10.1021/acs.joc.9b00928

Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines

J Org Chem. 2019 Aug 2;84(15):9778-9785. doi: 10.1021/acs.joc.9b00928. Epub 2019 Jul 23.

Authors

José M Gil-Negrete¹, José Pérez Sestelo¹, Luis A Sarandeses¹

Affiliation

¹ Centro de Investigaciones Científicas Avanzadas (CICA) and Departamento de Química , Universidade da Coruña , E-15071 A Coruña , Spain.

PMID: 31294552
DOI: 10.1021/acs.joc.9b00928

Abstract

Triorganoindium reagents (R₃In) react with tetrahydroisoquinolines (THIQs) in the presence of Ph₃CBF₄ as an oxidant to afford 1-substituted THIQs. The reaction proceeds in good yields at rt using 50 mol % R₃In with a variety of organic groups. ¹H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R₃In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.

Publication types

Research Support, Non-U.S. Gov't